diff --git a/lib/srv/desktop/rdp/rdpclient/src/rdpdr/filesystem.rs b/lib/srv/desktop/rdp/rdpclient/src/rdpdr/filesystem.rs
index 5210a704252e3..a954af5d0571e 100644
--- a/lib/srv/desktop/rdp/rdpclient/src/rdpdr/filesystem.rs
+++ b/lib/srv/desktop/rdp/rdpclient/src/rdpdr/filesystem.rs
@@ -79,6 +79,8 @@ impl FilesystemBackend {
         &mut self,
         res: efs::ServerDeviceAnnounceResponse,
     ) -> PduResult<()> {
+        // TODO(zmb3): send the underlying NTSTATUS code instead
+        // of converting everything to 0 or 1.
         let err_code = match res.result_code {
             NtStatus::SUCCESS => TdpErrCode::Nil,
             _ => TdpErrCode::Failed,
diff --git a/web/packages/teleport/src/lib/tdp/client.ts b/web/packages/teleport/src/lib/tdp/client.ts
index dc1496d68ec51..a415932b5e45c 100644
--- a/web/packages/teleport/src/lib/tdp/client.ts
+++ b/web/packages/teleport/src/lib/tdp/client.ts
@@ -397,10 +397,13 @@ export default class Client extends EventEmitterWebAuthnSender {
   handleSharedDirectoryAcknowledge(buffer: ArrayBuffer) {
     const ack = this.codec.decodeSharedDirectoryAcknowledge(buffer);
     if (ack.errCode !== SharedDirectoryErrCode.Nil) {
-      // TODO(zmb3): get a better error message here
-      this.handleError(
-        new Error(`Encountered shared directory error: ${ack.errCode}`),
-        TdpClientEvent.CLIENT_ERROR
+      // A failure in the acknowledge message means the directory
+      // share operation failed (likely due to server side configuration).
+      // Since this is not a fatal error, we emit a warning but otherwise
+      // keep the sesion alive.
+      this.handleWarning(
+        `Failed to share directory '${this.sdManager.getName()}', drive redirection may be disabled on the RDP server.`,
+        TdpClientEvent.TDP_WARNING
       );
       return;
     }
@@ -699,7 +702,8 @@ export default class Client extends EventEmitterWebAuthnSender {
     this.send(this.codec.encodeRdpResponsePDU(responseFrame));
   }
 
-  // Emits an errType event, closing the socket if the error was fatal.
+  // Emits an errType event and closes the websocket connection.
+  // Should only be used for fatal errors.
   private handleError(
     err: Error,
     errType: TdpClientEvent.TDP_ERROR | TdpClientEvent.CLIENT_ERROR
@@ -709,7 +713,7 @@ export default class Client extends EventEmitterWebAuthnSender {
     this.socket?.close();
   }
 
-  // Emits an warnType event
+  // Emits a warning event, but keeps the socket open.
   private handleWarning(
     warning: string,
     warnType: TdpClientEvent.TDP_WARNING | TdpClientEvent.CLIENT_WARNING